Molecular Recognition in Proton Transfer Compounds of Brucine with Achiral Substituted Salicylic Acid Analogues

Smith, Graham, Wermuth, Urs D., Healy, Peter J., & White, Jonathan M. (2006) Molecular Recognition in Proton Transfer Compounds of Brucine with Achiral Substituted Salicylic Acid Analogues. Australian Journal of Chemistry, 59(5), p. 328.

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The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 5-sulfosalicylic acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating brucine sheet host-substructures which incorporate interstitially hydrogen-bonded salicylate anion guest species and additionally in 3 the water molecules of solvation. The structure of 2 differs in having a three-centre brucinium–salicylate anion bidentate N+–H···O(carboxyl) hydrogenbonding association linking the species through interstitial associations involving also the water molecules of solvation. A review of the crystallographic structural literature on strychnine and brucine is also given.

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18 citations in Scopus
19 citations in Web of Science®
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ID Code: 4572
Item Type: Journal Article
Refereed: Yes
DOI: 10.1071/CH06074
ISSN: 0004-9425
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2006 CSIRO Publishing
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 12 Jan 2007 00:00
Last Modified: 29 Feb 2012 13:26

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